Director, Head of Analytics & Transformation, SMB

The Company

PayPal has been revolutionizing commerce globally for more than 25 years. Creating innovative experiences that make moving money, selling, and shopping simple, personalized, and secure, PayPal empowers consumers and businesses in approximately 200 markets to join and thrive in the global economy. 

We operate a global, two-sided network at scale that connects hundreds of millions of merchants and consumers. We help merchants and consumers connect, transact, and complete payments, whether they are online or in person. PayPal is more than a connection to third-party payment networks. We provide proprietary payment solutions accepted by merchants that enable the completion of payments on our platform on behalf of our customers.

We offer our customers the flexibility to use their accounts to purchase and receive payments for goods and services, as well as the ability to transfer and withdraw funds. We enable consumers to exchange funds more safely with merchants using a variety of funding sources, which may include a bank account, a PayPal or Venmo account balance, PayPal and Venmo branded credit products, a credit card, a debit card, certain cryptocurrencies, or other stored value products such as gift cards, and eligible credit card rewards.  Our PayPal, Venmo, and Xoom products also make it safer and simpler for friends and family to transfer funds to each other. We offer merchants an end-to-end payments solution that provides authorization and settlement capabilities, as well as instant access to funds and payouts. We also help merchants connect with their customers, process exchanges and returns, and manage risk. We enable consumers to engage in cross-border shopping and merchants to extend their global reach while reducing the complexity and friction involved in enabling cross-border trade. 

Our beliefs are the foundation for how we conduct business every day.  We live each day guided by our core values of Inclusion, Innovation, Collaboration, and Wellness. Together, our values ensure that we work together as one global team with our customers at the center of everything we do – and they push us to ensure we take care of ourselves, each other, and our communities.

Job Summary:

At PayPal, we are reinventing the way data and insights power the business decisions that drive growth for millions of small and medium-sized businesses (SMBs). We’re seeking a Director, Head of Analytics & Transformation to lead a multi-year evolution of our analytics function within the SMB division—from fragmented dashboards and manual reporting to a future where insights are automated, intelligent, and embedded directly into how decisions are made.

This is not a traditional analytics leadership role. You will both lay out the future vision of the analytics operating model while managing and standardizing the day to day operations of a large analytics team.

Establish a new operating model for insight consumption—one that includes proactive anomaly detection, narrative-driven reporting, and natural language insights delivered directly into tools like Slack and email.

Lead the SMB analytics team composed of analytics and data science professionals structured across several pods—ensuring that stakeholders like product managers and commercial leads, all the way up to business heads at the EVP level have access to high-quality, actionable insights that reflect the true state of the business.

Oversee and deliver executive-grade OKR tracking and reporting in the short term, supporting high-visibility business rhythms with precision and speed. Understanding the business is just as important as your technical chops.

Job Description:

What You’ll Own 

• Lead the transformation of our analytics operating model from static dashboards to a layered system of trusted data, shared metrics, and intelligent insight delivery. 

• Build and enforce a dashboard hierarchy (single → double → triple click) that ties every metric to strategic OKRs and downstream actionability. 

• Elevate our OKR reporting practice—initially through refined scripting, source alignment, and PowerPoint automation—while architecting the long-term shift to dynamic BI delivery (e.g., Looker Pulse, Slack-native reporting, AI-generated voiceovers). 

• Embed insights into the flow of work by partnering with LLM engineers and platform leads to drive Slack, email, and executive summary integrations. 

• Oversee three key pillars: 

• Product Analytics: responsible for defining and owning core product funnels (acquisition, activation, retention); partnering closely with Product and Engineering to identify drop-off drivers, design rigorous experimentation frameworks, and generate data-backed insights that inform roadmap prioritization, optimize conversion, and deepen understanding of user behavior across segments and journey 

• Commercial Analytics: responsible for end-to-end analysis of transaction activity, payment volumes, revenue, and margin across segments, channels, and products—delivering insight into business performance, partner impact, and monetization levers that drive growth and profitability. 

• Data & Analytics Enablement: Senior-level liaison into PayPal’s broader data infrastructure, tooling, and governance ecosystem. 

• Partner cross-functionally with business ops, finance, data engineering, and AI platform teams to influence tool adoption and insight accessibility. 

• Be a cultural driver for how we use data: shifting the organization away from “pulling dashboards” to “being alerted when it matters.” 

 

What We’re Looking For 

• 10+ years of experience in business analytics, data strategy, or data transformation roles, with a proven ability to lead through ambiguity. 

• Familiarity with the Google Analytics product suite (GCP, Looker Studio Pro / Looker Core, BQ, etc.) as well as integrations with various LLMs or other productivity tools (i.e. Slack, Teams, etc.) and how they support semantic modeling, real-time dashboards, and narrative reporting. 

• Strong executive communication and storytelling skills—you can translate noise into clarity for stakeholders at every level. 

• Experience leading multi-functional teams across product analytics, GTM/commercial analytics, and infrastructure liaison roles. 

• Demonstrated ability to evolve how insights are consumed—from manual PowerPoint decks to live dashboards, Slack alerts, and AI-generated summaries. 

• Comfortable collaborating with LLM engineers, data scientists, and platform teams, even if not building models directly. 

• High operational rigor: you bring structure and focus to dashboard sprawl, redundant queries, and fuzzy stakeholder asks. 

 

Preferred Qualification:

Preferred Qualifications 

• Experience leading analytics or reporting teams in fintech, payments, or enterprise-scale SaaS environments. 

• Familiarity with OKR methodologies and executive-level reporting cycles. 

• Exposure to AI-enhanced BI tools such as Looker Core, Looker Studio Pro, with GPT integration. 

• Experience working with distributed analytics teams, including offshore (e.g., India) collaboration models. 

 

Why This Role Matters 

This is a chance to fundamentally change how data drives decisions at one of the most impactful financial technology companies in the world. You’ll own both the vision and the execution path: from today’s reporting environment to tomorrow’s intelligent, contextual, and automated analytics experience. 

If you’re a builder, operator, and storyteller with strong data science underpinning, who’s excited by the challenge of scaling and modernizing a full stack data and analytics function in a global enterprise—we’d love to hear from you. 

Subsidiary:

PayPal

Travel Percent:

0

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PayPal is committed to fair and equitable compensation practices.

Actual Compensation is based on various factors including but not limited to work location, and relevant skills and experience.

The total compensation for this practice may include an annual performance bonus (or other incentive compensation, as applicable), equity, and medical, dental, vision, and other benefits. For more information, visit https://www.paypalbenefits.com.

The US national annual pay range for this role is $137,500 to $236,500

For the majority of employees, PayPal's balanced hybrid work model offers 3 days in the office for effective in-person collaboration and 2 days at your choice of either the PayPal office or your home workspace, ensuring that you equally have the benefits and conveniences of both locations.

Our Benefits:

At PayPal, we’re committed to building an equitable and inclusive global economy. And we can’t do this without our most important asset—you. That’s why we offer benefits to help you thrive in every stage of life. We champion your financial, physical, and mental health by offering valuable benefits and resources to help you care for the whole you.

We have great benefits including a flexible work environment, employee shares options, health and life insurance and more. To learn more about our benefits please visit https://www.paypalbenefits.com.

Who We Are:

Click Here to learn more about our culture and community.

Commitment to Diversity and Inclusion 

PayPal provides equal employment opportunity (EEO) to all persons regardless of age, color, national origin, citizenship status, physical or mental disability, race, religion, creed, gender, sex, pregnancy, sexual orientation, gender identity and/or expression, genetic information, marital status, status with regard to public assistance, veteran status, or any other characteristic protected by federal, state, or local law.  In addition, PayPal will provide reasonable accommodations for qualified individuals with disabilities.  If you are unable to submit an application because of incompatible assistive technology or a disability, please contact us at talentaccommodations@paypal.com.

Belonging at PayPal: 

Our employees are central to advancing our mission, and we strive to create an environment where everyone can do their best work with a sense of purpose and belonging. Belonging at PayPal means creating a workplace with a sense of acceptance and security where all employees feel included and valued. We are proud to have a diverse workforce reflective of the merchants, consumers, and communities that we serve, and we continue to take tangible actions to cultivate inclusivity and belonging at PayPal.

Any general requests for consideration of your skills, please Join our Talent Community.

We know the confidence gap and imposter syndrome can get in the way of meeting spectacular candidates. Please don’t hesitate to apply.